2 repeat Cy winners? It hasn't happened in 26 years

By Thomas Harrigan | February 27, 2026

Every era has its defining starting pitchers -- the aces who transcend their peers and become synonymous with a generation.

Right now, we’re in the epilogue of the era defined by Clayton Kershaw, Justin Verlander and Max Scherzer. A new crop of dominant arms has emerged, but we’re still waiting to see which hurlers earn generational status.

The 2026 season could be the inflection point.

Although there are many talented pitchers across the Majors, the Tigers’ Tarik Skubal and the Pirates’ Paul Skenes are operating on a different level than everyone else.

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Both pitchers essentially went wire to wire in their respective Cy Young races last season, entering the year as the consensus frontrunners and maintaining that status throughout the campaign.

Heading into 2026, nothing has changed -- they’re the favorites to repeat.

If they succeed, they'll accomplish something baseball has seen only once in the history of the Cy Young Award: two pitchers simultaneously winning back-to-back Cy Youngs.

The last time it happened? More than a quarter of a century ago, when Pedro Martinez and Randy Johnson pulled it off in 1999-2000. Looking back, there are some obvious parallels that stand out between then and now.

By the end of the 1990s, Martinez and Johnson were already well-established as iconic figures on Hall of Fame trajectories. But the 2000 season was pivotal nonetheless -- both won their third career Cy Young and put their status as timeless legends beyond question.

Skubal and Skenes stand at a similar juncture now, even if they aren't nearly as accomplished as Martinez and Johnson were going into 2000. They're already elite. But 2026 could be the season that transforms them into something greater.

As they prepare to pursue a share of history together, here's what's at stake for both pitchers on an individual level.

Skubal

What we haven't mentioned yet is that Skubal is actually going for his third consecutive American League Cy Young Award.

The left-hander captured his first after winning the AL's pitching Triple Crown with 18 wins, a 2.39 ERA and 228 strikeouts over 192 innings in 2024.

Skubal didn't repeat his Triple Crown feat last year but managed to improve slightly in a number of notable categories -- including ERA (2.21), K's (241), innings (195 1/3), FIP (2.45), WHIP (0.89) and K/BB ratio (7.30) -- en route to another Cy.

In the process, Skubal became just the 12th pitcher to win back-to-back Cy Young Awards. A third straight would put him in even rarer company -- Johnson (1999-2002) and Greg Maddux (1992-95) are the only pitchers to do it.

Consecutive or not, winning a third Cy Young would seriously elevate Skubal's Hall of Fame candidacy. Eleven pitchers have done it. Seven of them are enshrined in Cooperstown, and Kershaw, Verlander and Scherzer are likely to join them as soon as they're eligible. The only exception is Roger Clemens, who likely would have been a first-ballot pick if not for his link to PEDs.

Pitchers with at least three Cy Youngs

If the legacy ramifications weren't enough, this season also carries significant financial stakes for Skubal, who is entering his final year before free agency with a real chance to break Dodgers right-hander Yoshinobu Yamamoto's record for the richest contract (12 years, $325 million) signed by a pitcher in baseball history.

Skenes

Discussing a pitcher's legacy after just 55 career starts would normally be absurd. But there's nothing normal about what Skenes has done. His career is off to a nearly unprecedented start, and he has a chance to separate himself even further in 2026.

In 2025, Skenes became the fifth-youngest pitcher to win the Cy Young and joined Fernando Valenzuela (both in 1981) and Dwight Gooden (’85 and ’86) as the only pitchers to capture both the Rookie of the Year and Cy Young Awards within their first two seasons. No one has ever started off their career with a Rookie of the Year and two Cy Youngs over their first three seasons.

But the hardware only tells part of the story. Skenes has garnered those accolades while recording a 1.96 ERA, the lowest through 55 career starts of anyone in the Live Ball Era (since 1920).

Lowest ERA through 55 career starts
Live Ball Era (since 1920)

  1. Paul Skenes: 1.96
  2. Vida Blue: 2.04
  3. Howie Pollet: 2.07
  4. Orel Hershiser: 2.09
  5. Dwight Gooden: 2.12

Up next for Skenes? How about a third straight season with a sub-2.00 ERA?

Kershaw and Sandy Koufax are the only Live Ball Era pitchers to post three sub-2.00 ERA seasons (minimum 20-plus starts) at any point. No one has reeled off three such seasons consecutively, much less to start off a career.

Skenes could do all of that before turning 25. Skubal, meanwhile, is relatively young himself at 29. They both have a lot of good years ahead of them.

When all is said and done, though, we may look back on 2026 as the season they solidified themselves as the defining pitchers of this era.

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